CN105646831B - 一种松香基脂肪族聚氨酯预聚体的制备方法 - Google Patents
一种松香基脂肪族聚氨酯预聚体的制备方法 Download PDFInfo
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- CN105646831B CN105646831B CN201610138983.4A CN201610138983A CN105646831B CN 105646831 B CN105646831 B CN 105646831B CN 201610138983 A CN201610138983 A CN 201610138983A CN 105646831 B CN105646831 B CN 105646831B
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- rosin
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- abietyl
- acrylic acid
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- 239000004814 polyurethane Substances 0.000 title claims abstract description 14
- 229920000642 polymer Polymers 0.000 title claims abstract description 11
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 11
- 125000001931 aliphatic group Chemical group 0.000 title claims abstract description 4
- 238000002360 preparation method Methods 0.000 title claims abstract description 4
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims abstract description 45
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims abstract description 45
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims abstract description 45
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims abstract description 16
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims abstract description 15
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229920005862 polyol Polymers 0.000 claims abstract description 12
- 150000003077 polyols Chemical class 0.000 claims abstract description 12
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 60
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 238000004458 analytical method Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- DDKIXUQHRSUCMN-UHFFFAOYSA-N n-butylbutan-1-amine;propan-2-one Chemical compound CC(C)=O.CCCCNCCCC DDKIXUQHRSUCMN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 238000010792 warming Methods 0.000 claims description 5
- 238000007599 discharging Methods 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 239000011248 coating agent Substances 0.000 abstract description 6
- 238000000576 coating method Methods 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 4
- 239000010985 leather Substances 0.000 abstract description 3
- 238000007259 addition reaction Methods 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000011527 polyurethane coating Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/6705—Unsaturated polymers not provided for in the groups C08G18/671, C08G18/6795, C08G18/68 or C08G18/69
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
- C09F1/04—Chemical modification, e.g. esterification
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Polyurethanes Or Polyureas (AREA)
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CN201610138983.4A CN105646831B (zh) | 2016-03-13 | 2016-03-13 | 一种松香基脂肪族聚氨酯预聚体的制备方法 |
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CN201610138983.4A CN105646831B (zh) | 2016-03-13 | 2016-03-13 | 一种松香基脂肪族聚氨酯预聚体的制备方法 |
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CN105646831A CN105646831A (zh) | 2016-06-08 |
CN105646831B true CN105646831B (zh) | 2018-07-06 |
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Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN109265727B (zh) * | 2018-08-14 | 2020-11-24 | 桂林理工大学 | 一种松香基hdi型聚氨酯分子印迹微球的制备方法 |
CN110467716A (zh) * | 2019-08-01 | 2019-11-19 | 桂林理工大学 | 一种松香基hdi型抑菌聚氨酯的制备方法 |
CN113651922A (zh) * | 2021-07-17 | 2021-11-16 | 桂林理工大学 | 一种松香基荧光聚氨酯微球的制备方法 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3692720A (en) * | 1971-01-25 | 1972-09-19 | Hercules Inc | Resinous compositions from hydroxyalkylated rosin derivatives |
CN101497685A (zh) * | 2009-02-23 | 2009-08-05 | 中国林业科学研究院林产化学工业研究所 | 松香基水性聚氨酯的制备方法 |
CN101544744A (zh) * | 2009-04-17 | 2009-09-30 | 中国科学院广州化学研究所 | 丙烯酸松香环氧树脂预聚体及其制备方法 |
CN102659598A (zh) * | 2012-05-23 | 2012-09-12 | 桂林理工大学 | 利用松香与甲基丙烯酸缩水甘油酯制备酯化物的方法 |
CN102660193A (zh) * | 2012-05-12 | 2012-09-12 | 桂林理工大学 | 利用聚合松香与甲基丙烯酸羟基酯制备酯化物的方法 |
CN102702471A (zh) * | 2012-06-27 | 2012-10-03 | 惠州市汉诺新材料有限公司 | 一种无溶剂水性聚氨酯分散体的制备方法 |
CN102993685A (zh) * | 2012-11-23 | 2013-03-27 | 青岛文创科技有限公司 | 一种松香基水性聚氨酯丙烯酸酯复合乳液 |
-
2016
- 2016-03-13 CN CN201610138983.4A patent/CN105646831B/zh active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3692720A (en) * | 1971-01-25 | 1972-09-19 | Hercules Inc | Resinous compositions from hydroxyalkylated rosin derivatives |
CN101497685A (zh) * | 2009-02-23 | 2009-08-05 | 中国林业科学研究院林产化学工业研究所 | 松香基水性聚氨酯的制备方法 |
CN101544744A (zh) * | 2009-04-17 | 2009-09-30 | 中国科学院广州化学研究所 | 丙烯酸松香环氧树脂预聚体及其制备方法 |
CN102660193A (zh) * | 2012-05-12 | 2012-09-12 | 桂林理工大学 | 利用聚合松香与甲基丙烯酸羟基酯制备酯化物的方法 |
CN102659598A (zh) * | 2012-05-23 | 2012-09-12 | 桂林理工大学 | 利用松香与甲基丙烯酸缩水甘油酯制备酯化物的方法 |
CN102702471A (zh) * | 2012-06-27 | 2012-10-03 | 惠州市汉诺新材料有限公司 | 一种无溶剂水性聚氨酯分散体的制备方法 |
CN102993685A (zh) * | 2012-11-23 | 2013-03-27 | 青岛文创科技有限公司 | 一种松香基水性聚氨酯丙烯酸酯复合乳液 |
Non-Patent Citations (3)
Title |
---|
Preparation of Polystyrene Microspheres Using Rosin-Acrylic Acid Diester as a Cross-Linking Agent;Cai-li Yu等;《Industrial and Engineering Chemistry Research》;20140115;第53卷(第6期);2244-2250 * |
松香丙烯酸加成物与HEMA酯化及溴化反应研究;余彩莉 等;《中国胶粘剂》;20110131;第20卷(第1期);18-20 * |
松香和甲基丙烯酸缩水甘油酯酯化反应研究;任鹏 等;《化学研究与应用》;20140331;第26卷(第3期);427-431 * |
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Effective date of registration: 20210826 Address after: 210000 Fengshan Road, Gaochun Economic Development Zone, Nanjing, Jiangsu Patentee after: NANJING ZHENZHI NEW MATERIAL TECHNOLOGY Co.,Ltd. Address before: No.716, 7th floor, building 4, No.99 Guangfu Road, Wuhou District, Chengdu, Sichuan 610000 Patentee before: Chengdu yishenrui Technology Co.,Ltd. Effective date of registration: 20210826 Address after: No.716, 7th floor, building 4, No.99 Guangfu Road, Wuhou District, Chengdu, Sichuan 610000 Patentee after: Chengdu yishenrui Technology Co.,Ltd. Address before: 541004 the Guangxi Zhuang Autonomous Region Guilin Construction Road No. 12 Patentee before: GUILIN University OF TECHNOLOGY |